ChemicalBook CAS DataBase List 1,1-Bis(4-methoxyphenyl)-2-propyn-1-ol

1,1-Bis(4-methoxyphenyl)-2-propyn-1-ol synthesis

9synthesis methods

Product Name:1,1-Bis(4-methoxyphenyl)-2-propyn-1-ol
CAS Number:101597-25-5
Molecular formula:C17H16O3
Molecular Weight:268.31

The preparation of 1,1-bis(4-methoxyphenyl)-2-propyn-1-ol is as follows:18W % sodium acetylide in xylene/mineral oil 121.1mL (0.45mol, 1eq) was dissolved in anhydrous THF (1L) saturated with acetylene gas. After that 4,4-dimethoxybenzophenone 100g (0.41mol, 1eq) was put inside the reaction mixture under nitrogen and stirred for 24h at room temperature. The product was extracted by solvent extraction using ethyl acetate and water, organic layer was dried with MgSO4 and solid product on vacuum drier. After complete drying, the product again dissolve in ethyl acetate and poured into 1L hexane slowly under stirring which afford 8 as white color solid, yield (99g, 90%).

90-96-0 Synthesis

90-96-0
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4301-14-8 Synthesis

4301-14-8
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92298-55-0 Synthesis

tetraMethyl cyclohexane-1,2,4,5-tetracarboxylate

92298-55-0
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Yield:92298-55-0 91%

Reaction Conditions:

in tetrahydrofuran at 25 - 60; for 2 h;Inert atmosphere;

Steps:

23 4.3.23. 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, (18g)

Ethynylmagnesium bromide (4 mmol, 0.5?M in THF) was added to the suspension of ketone 15 (0.5?g, 2.0?mmol) in THF (2?mL) at 25?°C.
The mixture was then stirred at 60?°C for 2?h and then quenched with saturated aqueous NH₄Cl solution.
The aqueous layer was separated and extracted three times with Et₂O.
The combined organic fractions were washed with brine, dried over Na₂SO₄ and concentrated under reduced pressure.
The crude product was recrystallized from Et₂O/PE. White solid (490?mg, 91%).
Mp: 90-91?°C. IR (KBr): ?=?3472, 3245, 3004, 2959, 2932, 2836, 2545, 2102, 2039, 1933, 1902, 1886, 1870, 1683, 1635, 1607, 1584, 1506, 1464, 1455, 1440, 1415, 1350, 1305, 1295, 1251, 1241, 1199, 1180, 1164, 1199, 1180, 1164, 1119, 1062, 1025, 991, 967, 930, 897, 842, 882, 815, 782, 764, 732, 715, 685, 633, 627, 587, 526, 510, 488?cm^-1. ¹H NMR (500?MHz, CDCl₃) δ 2.79 (s, 1H), 2.86 (s, 1H), 3.79 (s, 6H), 6.83-6.89 (m, 4H), 7.47-7.53 (m, 4H) ppm. ¹³C NMR (126?MHz, CDCl₃) δ 55.42, 73.76, 75.22, 86.92, 113.68, 127.46, 137.06, 159.26?ppm. HRMS (EI): [M]⁺ calcd. for C₁₇H₁₆O₃, 268.1099; found: 268.1096.